methyl 1H-indazole-3-carboxylate → HCID 10680335, 화합물

HRID 1666059노트

반응식

HRID 1666059 반응식
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4].[CH3:14][C:15](C)([O-])[CH3:16].[K+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH:15]([CH3:16])[CH3:14])[N:6]=1)=[O:4]

참가 물질

4

반응물 2

HCID 657476methyl 1H-indazole-3-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 10680335HCID 10680335, 화합물수율 98.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of indazole-3-carboxylic acid methyl ester (40.7 g, 231 mmol) in anhydrous tetrahydrofuran (700 mL) cooled in an ice bath was added slowly solid potassium tert-butoxide (28.3 g, 252 mmol). The mixture was stirred at the same temperature for 1 hr prior to the addition of 2-iododopropane (34.4 mL, 367 mmol). The final mixture was stirred for 12 h at ambient temperature, and refluxed for 12 h. After cooling to room temperature, the mixture was filtered, and the collected solid was rinsed with tetrahydrofuran (100 mL). The filtrates were combined, and concentrated to dryness under reduced pressure, affording crude 1-isopropyl-1H-indazole-3-carboxylic acid methyl ester (49.7 g) as a pale yellow oil. The crude material was purified by flash silica gel chromatography eluting with hexane/ethyl acetate (9/1 to 3/1) to yield 1-isopropyl-1H-indazole-3-carboxylic acid methyl ester (43 g, 197 mmol, >99% pure). 1H-NMR (CD3OD, 300 MHz): δ (ppm) 8.1-8.0 (1H, d), 7.6 (1H, d), 7.4 (1H, t), 7.2 (1H, t), 5.0 (1H, quin), 3.9 (s, 3H), 1.5 (6H, d).

후처리

  1. additionto the addition of 2-iododopropane (34.4 mL, 367 mmol)
  2. temperaturerefluxed for 12 h
  3. filtrationthe mixture was filtered
  4. washthe collected solid was rinsed with tetrahydrofuran (100 mL)
  5. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-f4f250c3a4bc4d56a757012c76afc3e5
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044045B2

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